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■ Studies on as-Triazine Derivatives XIV. Synthesis and Reverse Electron-demand Diels-Alder Reaction of Ethyl 5,8-Dichloro-1,2,4-benzotriazine-3-carboxylate

Mataichi Sagi, Osamu Sato, Shoetsu Konno, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Ethyl 5,6,7,8-tetrahydro-1,2,4-benzotriazine-3-carboxylate was treated with sulfuryl chloride to give ethyl 5,5,8,8-tetrachloro-5,6,7,8-tetrahydro-1,2,4-benzotriazine-3-carboxylate. Following dehydrochlorination of the tetrachloro compound with triethylamine afforded ethyl 5,8-dichloro-1,2,4-benzotriazine-3-carboxylate. The dichloro-1,2,4-benzotriazine derivative was heated with norbornadiene in p-cymene to give ethyl 5,8-dichloroquinoline-2-carboxylate. Intramolecular Diels-Alder reaction of the dichloro-1,2,4-benzotriazine derivative was also investigated.